2-Methyl-3-furanthiol → 4-(2-Methyl-furan-3-ylsulfanyl)-5-nitro-thiophene-2-carboxylic acid methyl ester

HRID 2216025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2216025
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8](Br)[CH:9]=1)=[O:4].[CH3:14][C:15]1[O:16][CH:17]=[CH:18][C:19]=1[SH:20]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([S:20][C:19]2[CH:18]=[CH:17][O:16][C:15]=2[CH3:14])[CH:9]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 342862-Methyl-3-furanthiolHCID 13291027Methyl 4-bromo-5-nitrothiophene-2-carboxylate

Produkt 1

HCID 695867094-(2-Methyl-furan-3-ylsulfanyl)-5-nitro-thiophene-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Bromo-5-nitro-thiophene-2-carboxylic acid methyl ester ((Example 114, step c) 532 mg, 2 mmol), 2-methyl-furan-3-thiol (600 mg, 5.26 mmol), and DMAP-polystyrene resin (2 g, 2.86 mmol) were stirred in THF (10 mL) for 12 h at rt. The resin was filtered and washed with several portions of DCM (100 mL total volume). The filtrate was concentrated in vacuo and the yellow residue (480 mg, 80%) was used without further purification. 1H-NMR (CDCl3): δ 7.46 (d, 1H, J=1.9 Hz), 7.05 (s, 1H), 6.43 (d, 1H, J=1.9 Hz), 3.90 (s, 3H), 2.38 (s, 3H).

Aufarbeitung

  1. filtrationThe resin was filtered
  2. washwashed with several portions of DCM (100 mL total volume)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe yellow residue (480 mg, 80%) was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-c71413315d7a4606bc7b4efca0e06819
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109354B2

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